Highly Efficient Stereoconservative Amidation and Deamidation of α-Amino Acids

Deepak M. Shendage, Roland Fröhlich, and Günter Haufe*
Organisch-Chemisches Institut, Universitt Mnster, Corrensstrasse 40, D-48149 Mnster, Germany
Org. Lett., 2004, 6 (21), pp 3675–3678
DOI: 10.1021/ol048771l
Publication Date (Web): September 24, 2004
Copyright © 2004 American Chemical Society
*

 To whom correspondence should be addressed. Phone:  ++49-251-8333281. Fax:  ++49-251-83-39772.

, haufe@uni-muenster.de

Abstract

Abstract Image

An overall stereoconservative protection and deprotection method of amino and carboxyl groups is presented. N-Phthaloyl N-alkyl secondary amides of α-amino acids can be generated from corresponding N-phthaloyl amino acids by coupling reaction of N-alkylamines using mixed anhydride method. These secondary amides can be transformed by thermal rearrangement of intermediate nitrosoamides to O-alkyl esters with retention of configuration and excellent yields.

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History

  • Published In Issue October 14, 2004
  • Received June 28, 2004

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